The Charles River between the Harvard and Longfellow bridges

STAY IN THE REAL NEIGHBORHOOD
Formerly rough-and-tumble South Boston ("Southie" to Good Will Hunting fans) now has its share of top bistros, bars, and hotels. But the old neighborhood has retained enough hard-luck charm to feel distinct from boutique-ified Back Bay. Stay in the waterfront district's pioneer hotel, the swanky Seaport (rooms from $289; 617-385-4000, seaportboston.com). Legal Sea Foods opened a high-tech restaurant in June called LTK Bar & Kitchen that serves small-plate dishes such as tuna sashimi and a chicken-and-shrimp omelet with sweet chili sauce. Take your iPod and ask your waiter to bring a dock for the table (617-330-7430, ltkbarandkitchen.com).

LAY HANDS ON THE MONSTER
More of a shrine than a stadium, Fenway Park draws fans on pilgrimages even when the Red Sox aren't playing. Tours (yes, you can touch the Green Monster) run daily on the hour ($12; boston.redsox.mlb.com). If it's game day, try StubHub for tickets (866-788-2482, stubhub.com), because Fenway is perpetually sold out. Or watch from the bar at the Cask 'n' Flagon, a Sox fan stronghold right outside the stadium. Just show up at least an hour before the game starts to guarantee yourself a stool (617-536-4840).

PLAY LIKE THE LOCALS DO
Catch an eyeful of fall foliage from the Buck Hill trail in the 7,000-acre Blue Hills Reservation, a local hikers haven 20 minutes south of the city (617-698-1802, mass.gov/dcr/parks/metroboston/blue.htm). Or tap into the Hub's sailing subculture at Community Boating, which is located near the Charles Street footbridge. For novices, $80 buys two basic classes, which take about five hours, and a 30-day membership. After you've passed the course and a brief competency test, the windy Charles is all yours (617-523-1038, community-boating.org).

SAVOR A CULINARY REVOLUTION
Boston's pub-town reputation is fast changing as more big-name restaurateurs push for diversified (but still affordable) menus to satisfy the city's food-savvy crowds. Case in point: Garrett Harker's new Eastern Standard Kitchen and Drinks in Kenmore Square. Sit at the 40-foot-long marble bar in this lofty, art-deco setting and test your taste buds on the unctuous, foie gras-like roast bone marrow or a frisˇe salad with sweetbreads crowned with a perfectly poached egg (617-532-9100). If you'd rather stick to the basics, the Union Oyster House still wins for the best clam chowder, which it has been serving since 1826 (unionoysterhouse.com).